Technical Field
The present disclosure relates to gold(I) complexes with antiproliferative or antitumor activities. More specifically, these gold(I) complexes are gold(I)-carbenes having selones as co-ligands.
Description of the Related Art
The “background” description provided herein is for the purpose of generally presenting the context of the disclosure. Work of the presently named inventors, to the extent it is described in this background section, as well as aspects of the description which may not otherwise qualify as prior art at the time of filing, are neither expressly or impliedly admitted as prior art against the present disclosure.
Gold(I) compounds have been used for treatment of rheumatoid arthritis since the 1930s (J. Forestier, J. Lab. Clin. Med., 1935, 20, 827-840; and S. P. Fricker, Gold bulletin., 1996, 29, 53-60). Clinically prescribed anti-arthritis gold(I) complexes include gold(I) thiomalate (Myocrisin), gold(I) thioglucose (Solganol), and (2,3,4,6-tetra-O-acetyl-1-(thio-kS)-b-D-glucopyranosato)-(triethylphosphine)gold(I) (Auranofin) (C. F. Shaw III, Chem. Rev., 1999, 99, 2589-600; and S. Ahmad, A. A. Isab, S. Ali and A. R. Al-Arfaj, Polyhedron, 2006, 25, 1633-1645). In addition to anti-arthritic properties, some gold(I) complexes have demonstrated anticancer activities (M. Altaf, M. Monim-ul-Mehboob , M. Ogasawara , N. Casagrande, M. Celegato, C. Borghese, Z. H. Siddik, D. Aldinucci, A. A. Isab, Oncotarget, 2017, 8, 490-505; S.-H. G. Park, J. H. Lee, J. S. Berek and M. C.-T. Hu, Int. J. Oncol., 2014, 45, 1691-1698; K. K. Ooi, C. I. Yeo, K. P. Ang, A. M. Akita, Y. K. Cheah, S. N. A. Halim, H. L. Seng and E. R. T. Tiekink, J. Biol. Inorg. Chem., 2015, 20, 855-873; M. Ali, L. Dondaine, A. Adolle, C. Sampaio, F. Chotard, P. Richard, F. Denat, A. Bettaieb, P. Le Gendre, V. Laurens, C. Goze, C. Paul and E. Bodio, J. Med. Chem., 2015, 58, 4521-4528; J. D. Chaves, F. Neumann, T. M. Francisco, C. C. Correa, M. T. P. Lopes, H. Silva, A. P. S. Fontes and M. V. Almeida, Inorg. Chim. Acta, 2014, 414, 85-90; and A. A. A. Sulaiman, M. Altaf, A. A. Isab, A. Alawad, S. Altuwaijri and S. Ahmad, Z. Anorg. Allg. Chem., 2016, 642, 1454-1459, each incorporated herein by reference in their entirety). A good example is auranofin, which has undergone clinical trials for treatment of several types of cancer (W. Fiskus, N. Saba, M. Shen, M. Ghias, J. Liu, S. D. Gupta, L. Chauhan, R. Rao, S. Gunewardena, K. Schorno, C. P. Austin, K. Maddocks, J. Byrd, A. Melnick, P. Huang, A. Wiestner and K. N. Bhalla, Cancer Res., 2014, 74, 2520-2532; and X. Chen, X. Shi, C. Zhao, X. Li, X. Lan, S. Liu, H. Huang, N. Liu, S. Liao, D. Zang. W. Song, Q. Liu, B. Z. Carter, Q. P. Dou and X. Wang, J. I. Oncotarget, 2014, 5, 9118-9132, each incorporated herein by reference in their entirety). Furthermore, gold(I) complexes of N-heterocyclic carbenes (NHCs), especially gold(I)-NHCs derived from imidazolium and benzimidazolium salts, have been investigated in recent years (B. Bertrand and A. Casini, Dalton Trans., 2014, 43, 4209-4219; J. Weaver, S. Gaillard, C. Toye, S. Macpherson, S. P. Nolan and A. Riches, Chem. Eur. J., 2011, 17, 6620-6624; B. Bertrand, A. Citta, I. L. Franken, M. Picquet, A. Folda, V. Scalcon, M. P. Rigobello, P. Le Gendre, A. Casini and E. Bodio, J. Biol. Inorg. Chem., 2015, 20, 1005-1020; A. Pratesi, D. Cirri, M. D. Duovic, S. Pillozzi, G. Petroni, Z. D. Bugarcic and L. Messori, Biometals, 2016, 29, 905-911; L. Messori, L. Marchetti, L. Massai, F. Scaletti, A. Guerri, I. Landini, S. Nobili, G. Perrone, E. Mini, P. Leoni, M. Pasquali, and C. Gabbiani, Inorg. Chem., 2014, 53, 2396-2403; S. Gaillard, A. M. Z. Slawin and S. P. Nolan, Chem. Commun., 2010, 46, 2742-2744; O. Schuster, L. Yang, H. G. Raubenheimer and M. Albrecht, Chem. Rev., 2009, 109, 3445-3478; and X. Xu, S. H. Kim, X. Zhang, A. K. Das, H. Hirao and S. H. Hong, Organometallics, 2013, 32, 164-171, each incorporated herein by reference in their entirety). Due to their ability to form strong coordinate covalent bonds through σ-donation, carbene ligands form stable gold complexes (D. Marchione, L. Belpassi, G. Bistoni, A. Macchioni, F. Tarantelli and D. Zuccaccia, Organometallics, 2014, 33, 4200-4208; D. Benitez. N. D. Shapiro, E. Tkatchouk, Y. Wang, W. A. Goddard and F. D. Toste, Nature Chem., 2009, 1, 482-486; and L. N. D. S. Comprido, J. E. M. N. Klein, G. Knizia, J. Kastner and A. S. K. Hashmi, Angew. Chem, Int. Ed., 2015, 54, 10336-10340, each incorporated herein by reference in their entirety). Despite these recent advances, there remains a need to develop more efficient gold(I) anticancer agents.
In view of the forgoing, it is one objective of present disclosure to provide a therapeutic gold(I) complex with N-heterocyclic carbene and heterocyclic selone co-ligands and a method for treating cancer.